


The Bet.

by crusadingqueen



Category: Arrow (TV 2012)
Genre: Alternate Universe, Boss/Employee Relationship, Cunnilingus, Desk Sex, Explicit Sexual Content, F/M, Kissing, Rough Sex, Sexual Content
Language: English
Status: Completed
Published: 2015-06-08
Updated: 2015-06-13
Packaged: 2018-04-03 13:26:10
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 4,176
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4102624
Author URL: https://archiveofourown.org/users/crusadingqueen/pseuds/crusadingqueen
Summary: <blockquote class="userstuff">
              <p>There's a on going bet in the office and Felicity knows all about it.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> I was thinking of making this a three parts series, the next two parts would be with Sara and Tommy but that's only if you guys want me to.

 

                                                                                                            

 

Felicity had been aware of the bet that was going around the office for a while now and she knew she should be incredibly disgusted and angered by it since it was demeaning but she couldn't help but feel a bit flattered and aroused. They had a ongoing wager on who would be able to sleep with Felicity first. They're were three top canidates; Oliver Queen, Tommy Merlyn and Sara Lance.It definitely made her work life more interesting. With all there lingered touches, heated gazes and excessive flirting. It had been going on for months none of them having giving up yet. She had never considered sleeping with any of them, not that they weren't attractive because they definitely were but because it she was there boss and it would be terribly unprofessional. Under any other circumstance she would have had them in her bed long time ago.  At first she was able to keep her arousal at bay but as of late, fantasy involving them had been running rampant despite her best efforts.

Like tonight, she had to stay late to finish up some paperwork and she thought all her employees had gone home for the day. She could barely concentrate on signing her name, let alone reading the fine print on all the documents her mind was too clouded with lust. She imagined Oliver pumping into her as he pressed against the glass window where the world below if they just looked up could see her getting used, or Tommy taking on her desk and finally Sara bright blonde hair buried between her thighs. She couldn't stop herself, her right hand traveled beneath her skirt. Her index finger ghosted over the thin lace fabric that covered her cunt, she could feel her wetness seeping through her panties.  Her eyes fluttered as she gently pressed against her swollen clit, a shuddered breath escaped her parted lips.

'' Miss Smoak? ''

Her eyes flew open, her movement stilled.

She glanced up towards the door where Oliver Queen stood, in his three pieces charcoal grey suit. His piercing gaze pinning over to the chair, her skin flushed as heat washed over her.  It didn't matter that her large wood desk hid her action from his prying eyes, he knew what she had been doing.

'' M-Mr.Queen what are you doing here? '' She stammered, quickly retracting her hand from under her skirt.

'' I was wondering if you needed any help? '' Oliver asked lowly.

To anybody else, this could have sounded completely innocent but Felicity saw the way Oliver eyes darkened.

Felicity considered her answer carefully, she knew all the consequence this could entail but with the veil of arousal muddled her rational thoughts and she couldn't bring herself to care about the repercussion.

'' Yes '' She replied breathlessly.

Oliver smirked as he strode over towards her.

'' Get up '' He instructed huskily.

Slowly Felicity stood up on shaky legs and walked around her desk. Oliver took a step closer till his body was plastered to hers. The musky smell of his aftershave invaded her sense.

Oliver slid his other hand to cup the side of her neck, pulling her hard to his lips. He kissed her deeply, sliding his fingers to wrap tightly around the nape of her neck, her hair tickling his fingers. He squeezed firmly as their tongues battled together, flicking back and forth between their parted lips.She detected the taste of coffee and mint lingering on his tongue.  

His other hands curled around her waist and found the zipper at the back of her skirt. With one swift movement he tugged it down. Her skirt loosened around her hips and it only took one small movement to have the clothing fall to the floor. Oliver tore his mouth away from hers leaving her panting.

Oliver twirled his finger, '' Turn around and Bend over the desk ''

Felicity did as told, she quickly pushed away the paper that cluttered her desk so that she could rest lean against the wood.

'' God, your ass is perfect '' He said, tightly gripping the globes of flesh in his hands causing Felicity to gasp.

'' These need to go '' He purred as he slowly pulled her panties down her legs, his hands caressing the skin as he went before finally settling down on his knees.

'' God, I've been wanting to do this for so long '' He growled as he spread opened her cheeks. Felicity shivered violently as his warm breath fanned over her sex.

'' Spread your legs wider '' He commanded gruffly, Felicity didn't even hesitate.

He gave one deliberate lick along her slick, before nuzzling his face closer. His stubble scratched against the sensitive flesh of her inner thighs as he continued to lick into her.

'' Mmmm '' He hummed appreciatively, the vibration to her core cause Felicity to keen loudly.

His mouth was buried between her swollen folds, sucking on her pink clit and thrusting his tongue as deep as he could into her dripping sex.

Felicity bit down on her bottom lip so hard she could taste blood on her tongue as she desperately attempted to keep her moans at bay.

Oliver must have noticed because a second later his hand collided with her left cheek, she cried out as small tingles of pain mixed with arousal spread through her.

Oliver pulled away from her sex and stood up. Felicity could feel the whine build up in her throat but she harshly pressed her lips together. She couldn't have Oliver knowing how much he was effecting her and how desperate she truly was.

Oliver caught her earlobe between his teeth and nibbled playfully.

'' I want to hear you Felicity, I want to know how good I am making you feel, I want everyone who is still here to know how good I am fucking you '' He growled.

Felicity breath hitched at Oliver dirty words, she never even thought of the possibility of other employees lingering in the building hearing them.

But then, Oliver was  sliding his thick shaft back and forth between her puffy lips and her mind went blank.

Oliver gripped her hips tightly before sinking inside her tight channel.  Felicity head fell back against his shoulder as her mouth opened in a silent cry. His groans rumbled against her neck. She trembled at the sensation of fullness between her legs,

Oliver hand banded around her waist holding her place he pistoned into her. Her greedy walls clenched around her.

The crude sounds of their wet flesh smacking together reverberated off the office walls.

Oliver was giving her was enough to make her throw caution into the wind and swallow her pride.

'' Oh god.. Oliver! '' Felicity whined sharply,  when she felt the walls of her drenched cunt coil up tightly.

Her climax was without a doubt the most intense orgasm of her life. Her velvety walls fluttered wildly against his rock hard cock.

Oliver caught her as she slumped forward, her muscles turning to jell-o. He continued to fuck her, his thrust growing more erratic as he rapidly approached his own orgasm. He just needed a little push.

'' Cum insde me Oliver, come on '' She purred, her voice wrecked.

Oliver grunted and then stiffened against Felicity lush ass, spilling the rest of his hot seed into her tight cunt.

He buried his face in her neck as he panted, his hot breath fanning over her skin. He pressed a chaste kiss to her throat before pulling away.

She winced as he pulled out of her, the sudden emptiness all to much too soon. Her orgasm had taken up the little energy she had left. She lazily turned around to face Oliver.

She was surprised to see Oliver unbuttoning his suit jacket and shrugging it off.

'' Here's put this on. '' He gestured, before slipping over her shoulders.

It was very rare for Felicity to be at a loss for words, but at this moment she was. She brushed a wayward strand of hair that come apart from her ponytail behind her ears.

'' So what now? '' She asked, glancing up at him.

He was regarding her with a soft expression and reassuring smile, for a moment it felt like he was the boss and she was the employee.

'' First? How bout we take a nap on that awfully comfy look couch and then round 2 ? '' Oliver suggested, his smile morphing into a smirk.

The idea was more than appealing, she weighed her options carefully before replying '' Okay, but you can't tell anybody about this. If you want a round two nobody knows so that means not winning that bet. '' She said sternly, Oliver's eyes widened in surprises

'' You know about the bet?''  He asked guiltily.

'' Of course. I know everything ''

'' Really? ''

'' No, I heard you guys in the break room '' Felicity deadpanned, Oliver blushed crimson.

'' Oh! And I promise I won't tell anybody. ''


	2. Chapter 2

**Summary for the Chapter:**

> Oliver self-control snaps.

**Notes for the Chapter:**

> I was a bit overwhelmed by the amount of people that wanted a part two with Oliver! Hopefully this leaves up to your expectations. There will one last part that will be posted hopefully tomorrow. What do you want the third part to have? :)
> 
> I am leaving on vacation and I think a break from writing will do me some good, but I will be posted two more chapters on my Sacrifices fic. If any of you guys were interested :)
> 
> Thanks for reading.

Since that fateful night in Felicity office, Oliver couldn't get their encounter out of his mind. Every time he would walk into her office, he be assaulted by images of her bent of the desk, straddling him on the couch, and sucking him by the window. They had thoroughly christened every inch of that room. Unfortunately Felicity had wanted to keep thing strictly professional between the two, claiming that it was too risky. She hadn't spent years trying to gain the respects of her employees just to have it all taken away because she was horny. Oliver reluctantly agreed, despite that this had originally started out as a simple bet between his coworkers he had harbored a crush for his blond bespectacled boss since the moment he had met her.He had no intentions of telling Sara and Tommy about Felicity but he didn't want that night to only be a one time thing, he wanted _more_.

He had bitten his tongue the entire week as he watched her closely, she was taunting him with her low-cut blouses and skin-tight skirts and the way she would bend down in front of him or how her hand would linger on Tommy shoulder or how she would constantly be praising Sara good work. It was driving him mad.   
  
Oliver had never been a jealous person, but imagining Felicity with somebody else made him blood boil and he was having a hard time stifling him more primal urges. His self-control being pulled dangerously thin and on a Thursday morning in the elevator it snapped.

It was fitting that Tommy and Sara were both in the elevator when he got it, and a few second later Felicity followed. Her eyes immediately found his.

She offered them all a polite, '' Good morning '' before  placing herself in front of Oliver allowing more employers to shuffle into the lift. Her bright blond hair was pulled into a sleek ponytail and she had switched up her usual pencil skirt for cobalt blue dress.

Oliver had never been so grateful that they had to ride up 30 floors to get to their offices.   
  
Subtly Oliver took a step forward plastering himself to the back of Felicity, he immediately felt her tense but she remained silent. He smelt her signature scent a heady mix of floral and spice Oliver mouth watered she smelt delicious.

He slipped his hand between her thighs, he heard her gasp quietly as his warm hand came in contact with her skin. She immediately squeezed her thighs closed.

He brought his lips closer to her ear and whispered, '' Please '' Only she heard. Everybody in the lift was completely oblivious to what was happening only a few feet away from them. Even Sara and Tommy as they chatted among themselves.

He felt the pressure on his hand subsided as Felicity parted her thighs allowing him to guide his hand up higher. He rubbed over her panties before pushing the material to the side and slipping his finger between her folds.To his delight, Felicity was already wet. He spread the moisture along her slit and over her clit. He could hear her breathing quicken as his index finger swirled around her clit. He drew small eight figures around the sensitive bundle of nerves effectively bringing her higher and higher. He watched her closely he noticed that her hands trembling by her side and that she constantly nibbling on her bottom lip.

She was close he could tell, but then the elevator rang signaling that they had arrived on their floor. Oliver quickly withdrew his fingers and despite Felicity best efforts to keep quiet she whined catching Tommy and Sara attention. They turned around glancing at Felicity with concern.

'' Are you okay Miss Smoak? You look a bit flushed. '' Sara remarked.

'' Oh, I'm just feeling a bit ill, nothing an Advil won't fix. '' Felicity mumbled breathlessly. 

'' Okay. Well if you need anything I'm here '' Sara said with a smile, Oliver resisted the urge to roll his eyes. Give it up to Sara to be such an ass kisser. 

'' Thank you Miss. Lance '' Felicity said, with a warm smile. They all exited the elevator and went to their respective quarters but just before leaving Felicity turned around.

'' Mr.Queen, I need to see you in my office '' She instructed, to which he nodded keeping his feature schooled into neutrality so that Sara and Tommy couldn't detect his excitement but if they just looked down they would definitely witness his arousal.

He followed Felicity into her office, his eyes often trailing down to watch her plump ass sway.

Felicity shut the door behind them before turning around to glare at Oliver, '' What the hell were you thinking '' She snarled.

Oliver shrugged, '' I needed to touch you. ''

Felicity scoffed, '' You couldn't have waited till we were in private! ''

'' No. '' Oliver replied simply.

Felicity seemed taken aback by his answer, she narrowed her eyes at him '' Was this another bet ? '' She growled.

'' No! God no. '' Oliver assured her, Felicity shoulder slumped in relief.

'' You are more than just a bet to me Felicity '' He said softly, and he meant it.

Felicity didn't say anything for what felt like hours, and Oliver was starting to feel nervous maybe this was just a one time thing and Oliver had deluded himself Felicity had no desire of keeping Oliver around.

'' Okay... I believe but if we are going to do this, nobody can know. Not for now anyway. '' She said.

'' I can do that '' He promised, Being with Felicity was definitely more of a prize than winning a stupid bet.

'' Good. Now you owe me an orgasm '' Felicity purred.

Oliver grinned his cock straining against his slacks. He quickly unbuttoned his pants and pushed them to the floor.

'' On your knees baby '' He murmured, as he hooked his finger underneath the elastic and tugged off his boxer. His cock bobbed against his abdomen.

Felicity lowered herself to the floor and wrapped her hand around his length her thumb brushing over the bulbous head spreading the precum that had gathered there.  She stoked his cock languidly before leaning in and licking a stripe along the protruding vein than ran from the base to the tip.

Oliver groaned deeply. Felicity eyes flickered upward in warning reminding he needed to keep quiet. 

She slid his thick cock between her pouty pink lips. Her tongue running along the underside of his cock as she swallowed him deeper. 

Everytime she pulled back she would swirling her tongue along the sensitive tip.

His orgasm grew inside him, tingling at the base of spine as her mouth brought him closer to climax.

Suddenly she was cupping his balls, massaging them lightly.

Oliver choked out a , '' Felicity '' as his climax washed over him. His cock twitched inside her mouth before releasing his seed down her throat.

She pulled off him with a pop leaving his shaft glistening with saliva.She licked her lips and smoothed back her hair before standing up.

She smirked, '' That was fun, how bout we finish this after work '' She said taking his suit lapels between her fingers tugging him closer till her mouth was only inches away from his.

'' I'm dying to see you naked spread out on my bed '' She purred, her eyes gleaming mischievously.

It was easily the longest day of his life.


	3. Chapter 3

**Notes for the Chapter:**

> I actually wrote some of this in an airport talk about embarrassing, but I really wanted to get this up. So here you go, I know the ending isn't the best but hopefully you guys still enjoyed the final chapter :) xx thank you for reading.

Since the moment, Oliver exited her office time seemed to trickled by like molasses. Every time she'd glance at the clock, which was often, only a few minutes had passed. Usually focusing on work would make the day go by quicker by her mind kept drifting to Oliver. Everything from the sound that fell from his lips to the way his nose would scrunch up when he came. She was even considering quitting her day shorts and returning home immediately with Oliver but that would have risen way to much suspicion among her employers. Especially after the whole Elevator incident, she suspected that Tommy and Sara were already onto them.

So when five thirty rolled around, she couldn't leave quick enough.  When she  arrived in the underground parking lot she saw Oliver leaning against her car. Her gaze darted around anxiously but thankfully the lot was empty. She had spent the day imagining the things she would do to Oliver, or Oliver to her but in her imagination didn't do him justice. Standing with his suit jacket slung over his arm and his white buttoned down shirt sleeve rolled up revealing his surprisingly toned forearms.

'' Hi '' She murmured breathlessly.

'' Hi. '' He drawled, grinned down at her.  For a moment she just stared at him, sure she saw him almost everyday for the past three days but she always looked at him as an employee, she couldn't allow herself to see him as something more until now. Stuffing her hand in her purse she swiftly dug out her keys and offered them to him. She was too distracted at the moment it was better that she didn't get behind the wheel.

'' Do you want to drive? ''

'' Sure, '' Oliver acquiesced snatching the keys from her. He unlocked the door and opened the passenger seat letting Felicity slide into the vehicle before shutting the door behind her. A few seconds later he embarking into the driver seat.

Felicity thought the day passed by slowly, don't even get her started on the drive to her apartment.

She watched Oliver drive with his palm pressed the wheel as he efficiently and smoothly drifted through the streets of Starling.

When they finally arrived at Felicity place, Oliver barely had time to pull out the keys Felicity was opening his door and tugging him towards her apartment.

She couldn't resist the moment the lift door slide closed Felicity sealed her lips over Oliver. He reacted immediately pressing his body to hers as he walked her backwards until her back was against the wall, effectively pinning her in place as he ravished her mouth.

Olive smoothly rolled his hips against hers, His bulge pressing against the front of her dress.

'' Oliver, '' ' She gasped clutching his shoulders tightly.

'' I can't wait to be inside you '' He growled against her lips, before nipping at the bottom one playfully. His hand caressed her down her body coming down to rest behind her thighs.

'' Jump '' He commanded huskily. The familiar sound of the elevator rang in the ears and seconds later the doors were opening.

She surged upward wrapping her legs securely  around his narrow hips as he guided them to her apartment.

'' It's the last door, it's the gold key '' She mumbled, her fingers carding through his cropped locks as she nibbled on his jaw.

Oliver groaning, fumbled with her keys attempting to find the right one. Once he found it he quickly unlocked the door and tumbled into her hallway.

Blindly she reached for the light, flicking it on.

'' Where the bedroom? '' Oliver asked, glancing around.

'' To your left '' Felicity replied.

Once Oliver had found her bedroom he deposited her on the king size bed. she leaned up and started unbuttoning his shirt. Felicity was  patience was wearing thin so with one quick tug, the shirt tore open and the buttons scattered to the floor. She looked up at Oliver with a sheepish expression.

'' You have more of those I hope. '' She said apologetically. 

Oliver chuckled lightly , '' A ton more.. '' he assured her.

She was stricken by Oliver expression, it wasn't all hunger. She detected something else as well a softness she had yet to see.

'' Felicity.. '' Oliver whispered, regaining her attention.

'' Oh.. um. sorry '' she mumbled embarrassed, a flush spreading across her cheeks.

With shaky hands she undid his pants and pulled them downward, his boxer followed. She admired Oliver naked form for a moment before motioning towards the bed.

'' Lay down. '' She instructed.

He crawled up the bed until his head rested against the pillow, his eyes glued to her.

Felicity stood up and turned around so that her back was to Oliver. She slowly tugged down the zipper to her dress, the fabric loosened around her before falling to the floor.

'' Fuck, you're beautiful '' Oliver breathed. Felicity giggled as she reached behind her and unhooked her bra she tossed it across the room, her panties followed.

'' Christ, Come here, please. '' Oliver whimpered, as he his hand lazily stroked his hard length.

Felicity made her way to him to straddle his hips, his cock sliding between her slick folds.

Oliver hands immediately gravitated towards her hips clutching them tightly.

'' Felicity, please, do something '' Oliver mumbled, his fingers flexing with restraint.

Raising on her knees she gripped his pulsating cock between her hands and guided it to her core.  His blunt tip teased her entrance before she gently sank down onto his cock.

They groaned in unison. Felicity relishing in the fullness that Oliver created inside her.

''  You feel so fucking good around me, '' Oliver purred, as Felicity raised up before falling back down.

Felicity moaned as she started bouncing, Oliver sat up his hand banding around her hips as he attached his lips to her nipple. He suckled on the puckered nub adding to the sensation that was beginning to bloom her core.

Oliver tore his mouth away from her breasts and looked up at her. There heated gaze interlocked. The intensity between them heightened and Felicity couldn't look away.

Her nails dug into the skin of his back, surely leaving scarlet marks on the tanned flesh. He didn't seem to mind.

'' Ah.. Oliver .. '' Felicity sighed, rocking her hips frantically. A thin sheen of sweat glistened over their scorching bodies.

Oliver fingers found her clit, firmly drawing fast circles around the sensitive bundle of nerves. Felicity shuddered violently as she climaxed. Her orgasm washing through her in waves, as Oliver continued to buck his hips into hers.

Her muscles clenched hard around his cock coating it in her juices that dripped all the way down his thick base.

Oliver held her tightly against his chest as he erupted inside of her.

She crawled off Oliver and laid back on her the bed her body twitched from her aftershock of her orgasm.

'' Wow. '' Felicity murmured, relaxing back into the mattress.

Suddenly, Oliver was settling himself between her thighs. Gently he pushed her creamy thighs apart and leaned in his mouth lingering only a few inches away from her core.

'' Oliver.. what are you... '' She trailed off as Oliver tongue invaded her folds. Many men found the thought of eating cum repelling, especially their own but Oliver didn't seem bothered by it one bit. He was eagerly eating her out, his tongue alternating between flicking her clit and delving into her saturated channel. She should never compare Oliver  to another person, he was definitely one of a kind.

It didn't take very long, that Felicity was withering beneath his tongue, reaching her second orgasm.

When Oliver finally pulled away she was still panting, her slick skin sticking to the satin sheets.

Oliver laid down and gathered her into his arms.

'' Well you definitely won that bet.. '' Felicity mumbled sleepily.

'' What do you mean? '' Oliver inquired.

'' You didn't just fuck me first, but you can fuck me whenever you want. '' Felicity teased.

Oliver remained quiet for a moment, tilting his head pensively.

'' I don't just want this '' He gestured between their bodies, '' to be about fucking. This was never about the bet. I wanted you since the moment I laid eyes on you. '' Oliver admitted, and even in the darkness of the room Felicity detected a slight blush tinting his cheeks.

Felicity grinned, '' Good, so did I. Now we just need to figure out way to make this work. ''

Oliver kissed her softly, '' We'll figure it out together ''

And they did. It definitely wasn't easy they're relationship had to remain a secret for almost six months before Oliver quit his job since he had been offered a better position at another job.  Felicity missed having Oliver around but his departure also meant that they could finally go public. They waited a few months before announcing it and of course Tommy and Sara already knew. To Felicity embarrassment they had known since the elevator incident....


End file.
